Bromine → Sodium

HRID 1605493Notes

Reaction equation

HRID 1605493 reaction equation
[Na:1].[CH3:2][CH2:3][C@@H:4]([C:23]([C@H:25]([C@@H:27]([OH:43])[C@@H:28]([CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[C:34]([OH:39])[C:33]=1[C:40]([OH:42])=[O:41])[CH3:29])[CH3:26])=[O:24])[C@H:5]1[O:9][C@@:8]([C@@H:12]2[O:17][C@@H:16]([CH3:18])[C@@:15]([OH:21])([CH2:19][CH3:20])[CH2:14][CH2:13]2)([CH2:10][CH3:11])[CH2:7][C@@H:6]1[CH3:22].[Br:44]Br>C(=S)=S>[Br:44][C:37]1[C:32]([CH2:31][CH2:30][CH:28]([CH3:29])[CH:27]([OH:43])[CH:25]([CH3:26])[C:23](=[O:24])[CH:4]([CH2:3][CH3:2])[CH:5]2[CH:6]([CH3:22])[CH2:7][C:8]([CH2:10][CH3:11])([CH:12]3[CH2:13][CH2:14][C:15]([CH2:19][CH3:20])([OH:21])[CH:16]([CH3:18])[O:17]3)[O:9]2)=[C:33]([C:40]([OH:42])=[O:41])[C:34]([OH:39])=[C:35]([CH3:38])[CH:36]=1.[Na:1]

Participants

6

Reactant 3

HCID 24408BromineHCID 5360545SodiumHCID 5360807Lasalocid

Product 2

HCID 5360545SodiumHCID 23277601HCID 23277601, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a solution of 1.53 g of the sodium salt of antibiotic X-537A in 30 ml carbon disulfide was added dropwise a solution of 0.14 ml bromine 10 ml carbon disulfide at -5° over 10 minutes. The solvent was removed under a stream of nitrogen at room temperature (approximately 2 hours). The residue was purified by dissolving it in ethyl acetate and the solution washed successively with aqueous sodium bisulfite and sodium carbonate. After drying (Na2SO4), the solution was evaporated under reduced pressure and the residue crystallized from ethyl acetate to give 5-bromo-3-methyl-6-{7-ethyl-4-hydroxy-3,5-dimethyl-6-oxo-7-[5-ethyl-3-methyl-5-(5-ethyl-5-hydroxy-6-methyl-2-tetrahydropyranyl)-2-tetrahydrofuryl]heptyl} salicylic acid, sodium salt as colorless cubes, m.p. 185°, [α]D25 -7.36° (1% in methanol).

Workup

  1. customThe solvent was removed under a stream of nitrogen at room temperature (approximately 2 hours)
  2. customThe residue was purified
  3. dissolutionby dissolving it in ethyl acetate
  4. washthe solution washed successively with aqueous sodium bisulfite and sodium carbonate
  5. dry with materialAfter drying (Na2SO4)
  6. customthe solution was evaporated under reduced pressure
  7. customthe residue crystallized from ethyl acetate

Sources & evidence

ORD record
ord-cc57a6aaee8646ec9cce97fb99a762ba
Source dataset
uspto-grants-1976_04
Patent number
US03950320

Reaction notes

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